Alvin and the chipmunks Fanfic: The life of a Chipmunk
by Amunkman
Summary: The relationship between the Chipmunks and Chipettes increase day by day, until a chipmunk reveals his feelings for a chipette. What will happen between the other 4, including Dave? Update:(When released, read the update section for chapter 2 for clarification on certain aspects that has been mentioned to me through review).
1. First confessions

**All credits of Alvin and the Chipmunks goes to Ross Bagdasarian Sr. and because i am referring to the CGI film, credits also go to 20th Century Fox.**

 _A few months after the international music awards from Chipwrecked…_

Alvin, Simon, and Theodore are in the living room, about to watch a movie, "Who wants some cheese balls?" asks Alvin as he makes his way off the couch and into the kitchen. "oh, oh me!" exclaimed Theodore trailing behind him. Simon stays behind and goes to check on the Chipettes, in specific, Jeanette…

Simon leans near the door frame and finds the Chipettes going about their casual business with Dave in the next room thinking of ideas for a new song. *Now is not the time to tell her how I really feel about her* thinks Simon, heading back to the living room and surprisingly finds Alvin and Theodore watching meerkat manor… "Just like the old times huh," asks Simon, not expecting an answer. "Oh please, we all know that Theodore can't last a minute into horror movies" teased Alvin turning back to Theodore who was still calm.

Dave comes downstairs calling the chipmunks for dinner with the Chipettes being right behind him. Alvin sits facing Brittany, and to his left, Simon is facing Jeanette, and on Alvin's right Theodore is facing Eleanor.

Simon smiles at Jeanette, and Theodore licks his mouth area to show that he is ready to eat. "You are having biscuits and chicken today," Dave said. "Yum my favorite!" Theodore replied making Eleanor giggle.

Alvin finishes first but leaves leftovers (because he already ate cheese balls) and gives it to Theodore who agrees to take it; Eleanor finishes up and talks to Brittany, who finished a while ago.

Jeanette's esteem seemed a bit low and Simon told Dave about her noticing it. "well why don't you go and ask her to see if she is OK?" Dave replied… Simon took the job and when Jeannette finished she goes straight to her bed, not knowing that Simon was behind.

She turns around and gets startled, "oh-hey Simon," she says to which Simon says "h-hey Jeanette, how are you feeling?" she replies "have you ever thought what it would be like for our career to end?" Simon was shocked and he felt the need to comfort her...

"It's too early to be thinking about that, I mean, everyone loves us" he continues "you know, to me you are the star of the show, without you in my life I would not know what to do" "oh um, thanks," Jeanette says cheerfully. "Jeanette, will you be my girlfriend?" Simon requests, and Jeanette, without hesitation, says "Sure, that would be a nice thing"...

Simon gets up and kisses her on the cheek saying, "thank you" before heading downstairs to where the remaining chipmunks and Chipettes were. "So Si, what was happening up there?" asked Alvin with curiosity to which Simon said "w-we just talked that's all, she'll be resting upstairs, however"

Dave put on a bearable tv show for the chipmunks and Chipettes, then putting Simon aside. "Well how did it go?" asked Dave contently, "well uh heh, I have something surprising to tell you" begins Simon. "go on," says Dave urging Simon to continue...

"Jeanette and I are dating," says Simon in a rushed tone; Dave was blinking his eyes repeatedly but still replied "really? that's great news" he continues "but when are you planning to tell the others?" "Oh, uh I was thinking you could help out with that" Simon replied in a nervous way "Well when would you like to tell them?" asked Dave "Maybe right now, it's better to get this over with," Simon stated, clearly looking nervous...

Dave and Simon walked into the living room "How are you guys doing?" Theodore and Eleanor laugh at the tv show. "Look, guys, Simon has an announcement," Dave says while Simon climbs onto the table. Just when he was about to speak, Jeanette walks in and smiles, going onto the table where Simon was "well um, Simon and I are dating" Jeanette said feeling both nervous and confident...

"we're very happy for you," says Britany wishing she had the same thing going on, just like the current couple. "yeah" Theodore and Eleanor agreed, looking at each other for about 4 seconds. "So that was what you were doing this time," says Alvin in a Joking manner. Dave looks at him in a way "Fine fine congratulations bro, you deserve it" Alvin corrected himself after the look that dave gave him.

Simon and Jeanette hugged each other to know that they have no secret with each other. Theodore speaks up and now all the Attention was left at him "Um, Eleanor, uh I had feelings for you since the time I met you" "Oh Theo" Eleanor says smiling. He continues "I never had the courage to ask this but, would you like to be my girlfriend?" "Of course Theodore! I want that" Eleanor replies in the happiest state ever while giggling. They first hug then kiss "You go Theo" "Yeah you did it" Alvin and Simon both say one after the other"

"Well you both did have the courage to step up and confess to one another," Dave remarked, trying to encourage them "Since we are still on break from school, how about we go on a trip" "Really!?" everyone else exclaimed "yeah, and you each get your own rooms" He finishes off "Thanks, Dave" The Chipmunks and Chipettes say excitedly. This was going to be a long weekend.

 **Please note that this is my first story (Chapter) and i may have some sentence mistakes that i have not picked up on while rereading the story. I did my best and went through all the stages. But anyway, please comment what you want to see next. As mentioned at the beginning of the story All credits of Alvin and the Chipmunks goes to Ross Bagdasarian Sr. and because i am referring to the CGI film, credits also go to 20th Century Fox. I am a heavy fan of the Chipmunks and Chipettes so expect most of the stories i make about them. This is also a Fan Fiction so nothing that is in this story is actually in the movies or TV shows. Thank you for reading.**


	2. Postponed Love

"Who's ready for the trip," asked Dave in his original clothing, his clothes all packed up. "We are," the Chipmunks and Chipettes replied with excitement. "I wonder how this place is going to look like" "I can't wait!" "It'll be so much fun" They were all comments coming from Brittany, Jeanette, and Eleanor. Alvin, Simon, and Theodore were talking about what would be in their possession and what would not while being surrounded by suitcases. "Hold on guys, stop what you are doing" they stopped...

"You will all have different rooms, some of you will be ok and some will ... let's just say not" Dave continued "Simon and Jeanette, you will be in one room" Simon and Jeanette exchange Hugs "Theodore and Eleanor will be in another" They both high five each other "and Alvin, Brittany-you will be in separate rooms". "That's fine with me," said Alvin "I mean, I get a whole room to myself!" "Yeah," Said Brittany, part sad and part fine with the situation.

"Well I'm glad you guys are ok with it," said Dave as he put their luggage together. "Ok, the taxi should be here by now," said Dave walking and opening the door for the Chipmunks and Chipettes to get through. He closed the door and put the bags in the back of the car. He got inside, and they go to the Airport for a flight.

They get to their destination in nearly 2 days

"That was a long taxi ride!" said Alvin still waking himself up "Remember the flight," Simon added, "Its what took us the longest". "I'm tired," Theodore said with a little frown...

"Your not the only one," spoke Eleanor showing Brittany and Jeanette...

They stopped at the square, "Woah, where are we?" asked Jeanette filled with wonder "This place is beautiful" Brittany said agreeing with Jeanette. The place was filled with all types of people dressed in clothing that showed they had busy occupations. Dave spoke up "What you guys are seeing here is in New York City" he continues "We will check in to our hotel and we will talk about our schedule for vacation"...

Once checking into their rooms, the Chipmunks with the Chipettes get comfortable. Dave takes a nap from trying to make up a schedule. Once done, Simon and Theodore go into Alvin's room to have a talk.

"Well, how are you with this separate room thing?" asked Simon checking on Alvin. "Uh, great! I'm alone and have no one to talk to" said Alvin sarcastically. "so you do like Brittany, do you?" Theodore asked, "I guess I do" Alvin stated. "I just wonder how she will react, especially since I made an impression two days ago saying that I'm too cool for relationships". "Oh, that's harsh," said Simon. "It's not too late though," Theodore said assuredly "Dave might give you two a room, and if you need help, we will be there".

 _Inside Brittany's room..._

"I can't believe that it's me that has to be on my own" Brittany spoke up, whimpering. "It's only because we are in relationships, you can't just be with Alvin in a room out of nowhere," Jeanette replied, hoping she would understand. "Woah, woah, woah, I never said that I liked Alvin," Brittany said with a don't assume expression. "I'm sure that Alvin has feelings for you, he's just not ready to show it" Eleanor added, "Even Theodore was able to show his feelings in front of everyone, what is the difference?" Brittany asks, becoming confused.

It's time for lunch, but before the Chipmunks and Chipettes go downstairs, Dave speaks to them about their schedule. They will be staying in the hotel today, then go explore the city the next day, and so forth.

They go downstairs to the lobby and head towards the cafeteria to get their food. They get in line and then when it was their turn, they order a sandwich and sit down the way they do at home.

A fan notices them and comes to say "Congratulations on the award" and "what are you planning to do now?" Dave goes to talk to the fan so that the Chipmunks and Chipettes have their privacy.

"How are you feeling," Alvin asks Brittany "I'm doing fine" she mumbles to herself not knowing that her expression says otherwise. "I can tell," Alvin replies quizzically checking if she would see her mistake.

They finished off and went back to their assigned rooms as Dave had previously put it at the beginning of the trip. The chipmunks stay in Alvin's room and the Chipettes, in Brittany's room.

"When do you think you will tell Brittany how you feel?" Theodore asks Alvin while climbing unto the bed to where Alvin and Simon were. "Well let's see, we're outside and eating at a restaurant; somewhere during the week" Alvin replies not completely sure of what he was saying. It was 3 pm and Alvin was already tired. He requested to go to sleep and the remaining two stay in Alvin's room until he wakes back up.

 _A few hours later when it's 7 pm..._

Alvin wakes up and looks around and finds only one of his brothers next to him. He wakes Theodore up. "Y-Yeah?" Theodore says shakily. "Where's Simon?" Alvin says with question. Theodore looks around to see that Alvin was right. "I don't know," Theodore says now fully awake. This was one of the times that Theodore did not have a nightmare, but that was because he was with his brother.

Alvin and Theodore arrive at the door. "Simon," Alvin says in a lengthened tone. "Yeah?" Simon said in a muffled tone followed by the door opening to let the brothers in. "Why did you leave?" Theodore asks. "Oh, I wasn't tired so I let you guys sleep" Simon replied.

Meanwhile, Dave knocks on each door saying that it is time for bed because they were going to start going places the next day. He found most of them locked because the Chipmunks and Chipettes were using two different rooms. He opens the hotel door for Simon's room "Hey guys, it's time for bed" Dave announced, "You have 15 minutes until lights out". Alvin and Theodore go to sleep in their room for the next day. Eleanor caught up with Theodore and Both entered their assigned hotel room. The same happened with Simon and Jeanette. They all thought about the next day.

 _The next day..._

Dave woke up earlier than all the others. He let them sleep so that their energy can be refilled. He first checked Theodore and Eleanor's room only to find them cuddled together. This left the impression that Theodore had a nightmare and Eleanor had to care for him, but it was all under control. He woke them up and sent them down for breakfast where every other person in the hotel was.

"Simon, Jeanette, it's time for breakfast" Dave added on "today is the day we are going places". At this thought, Simon woke up and woke up Jeanette "Where are we going?" She asked curiously. "Go get breakfast and you'll see" Dave replied. They went down, now Dave has only two more people to wake up. Alvin's room was up ahead and Brittanys was on the other side. They both meant the opposite but they would still understand each other Dave thought.

Dave went back to wake up Brittany, then Alvin. They then headed downstairs. Alvin sat in between his brothers where they were. They finished eating and Dave took them to the same square they saw last time. Dave took them to the Empire State building as a surprise and he wanted to see the Chipmunks and Chipettes' reaction. They did not know that but when they got out of the cab, they were completely amazed "wow" said Alvin and Brittany, they looked at each other then looked away. "This place is awesome," Simon tells Dave. "Yeah," Jeanette says, agreeing with Simon. "Well, this is one of the many sights you will see," Dave smiled and went inside with the others for a tour.

At nearly 1 pm Dave, the Chipmunks, and Chipettes head to a restaurant...

Dave goes and sits down two at each table and to Alvin's request, he sits Alvin and Brittany at one table. "Don't hurt each other okay?" Dave asks to which they respond "yes". He takes the order of the pair and takes the order of the Simon, Jeanette, Theodore, and Eleanor.

"How are you feeling," Alvin starts off the conversation. "well, what do you think?" Brittany responds. "You look interested," Alvin says observantly. Brittany says a bit surprised "Yeah, but are you flirting with me?" "No" "look, I'm not ready for this" Brittany says to Alvin becoming a bit nervous. Alvin became shocked and so did Simon too when he heard that. They finished eating in silence and they headed back to the hotel. Alvin was going to have to try again.

 **(Update: I am aware that Road chip already came out but i decided to write after chip-wrecked because then this is how i imagined my story to be. After this series of stories, i might do something on Bringing back the chipettes from where they left in road chip. Thanks for bringing this into my Attention). Please note that this is my first story and i may have some sentence mistakes that i have not picked up on while rereading the story. I did my best and went through all the stages. But anyway, please comment what you want to see next. All credits of Alvin and the Chipmunks goes to Ross Bagdasarian Sr. and because i am referring to the CGI film, credits also go to 20th Century Fox. I am a heavy fan of the Chipmunks and Chipettes so expect most of the stories i make about them. This is also a Fan Fiction so nothing that is in this story is actually in the movies or TV shows. Thank you for reading.**


End file.
